Anti-hepatitis B virus active phenylpropanoids adamantine ketoxime ester compound

A technology of phenylpropanoid adamantanone oxime and ester compounds, which is applied in the fields of antiviral agents, oxime preparation, organic chemistry, etc., and can solve drug withdrawal rebound, nucleoside analog drug resistance, and endanger the effect of hepatitis B virus vaccine And other issues

Inactive Publication Date: 2015-06-10
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, nucleoside analogs generally have drug resistance and drug withdrawal rebound problems, and the use of nucleoside drugs also endangers the effect of hepatitis B virus vaccine

Method used

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  • Anti-hepatitis B virus active phenylpropanoids adamantine ketoxime ester compound

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Experimental program
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Effect test

Embodiment 1

[0049] The preparation method of the first phenylpropanoid oxime ester compound 3,4-dimethoxycinnamic acid-2'-adamantanone oxime ester, the steps are as follows:

[0050] (1) Add 10 mmol of adamantanone, 12 mmol of hydroxylamine hydrochloride, 12 mmol of sodium acetate trihydrate, and finally add 50 ml of ethanol to dissolve, and stir and react at 60° C. for 2 hours. After stopping the reaction, the solution was concentrated to remove ethanol to obtain a concentrate. The concentrate was dissolved in 50 ml of dichloromethane, washed three times with 70 ml of hydrochloric acid solution with a concentration of 1 mol / L, and the upper layer solution was separated and removed to obtain the lower layer of dichloromethane solution. After acid washing, the dichloromethane solution was washed three times with 70 ml of water, and then the lower dichloromethane solution was separated. The dichloromethane solution washed with water was finally washed three times with 70 ml of saturated aq...

Embodiment 2

[0054] The preparation method of the second phenylpropanoid oxime ester compound 3,4,5-trimethoxycinnamic acid-2'-adamantanone oxime ester, the steps are as follows:

[0055] (1) Same as step (1) of Example 1.

[0056] (2) Dissolve 10mmol of 3,4,5-trimethoxycinnamic acid in 10ml of dichloromethane, add 50mmol of thionyl chloride, stir and reflux at 65°C for 5 hours, stop the reaction and concentrate to obtain 3, 4,5-Trimethoxycinnamoyl chloride.

[0057] (3) Dissolve the 2-adamantanone oxime prepared in step (1) in 15 milliliters of dichloromethane, add 12 mmol of triethylamine and 12 mmol of 3,4,5-trimethoxy Cinnamoyl chloride, after reacting at 0°C for 30 minutes, then continue to react at room temperature for 12 hours, stop the reaction, concentrate under reduced pressure, and separate by silica gel column chromatography. The mobile phase is composed of petroleum ether with a boiling point of 60-90°C: The volume ratio of ethyl acetate was gradually changed from 4:1 to 1.5...

Embodiment 3

[0059] The preparation method of the third phenylpropanoid oxime ester compound 3,4-(methylenedioxy)cinnamic acid-2'-adamantanone oxime ester, the steps are as follows:

[0060] (1) Same as step (1) of Example 1.

[0061] (2) Dissolve 10mmol of 3,4-(methylenedioxy)cinnamic acid in 10ml of dichloromethane, add 50mmol of thionyl chloride, stir and reflux at 65°C for 5 hours, stop the reaction and concentrate to obtain 3,4-(Methylenedioxy)cinnamoyl.

[0062](3) Dissolve the 2-adamantanone oxime prepared in step (1) in 15 milliliters of dichloromethane, add 12 mmol of triethylamine and 12 mmol of 3,4-(methylenedioxy ) cinnamoyl chloride, after reacting at 0°C for 30 minutes, then continue to react at room temperature for 12 hours, stop the reaction, concentrate under reduced pressure, and separate by silica gel column chromatography. The mobile phase is composed of petroleum ether with a boiling point of 60-90°C : The volume ratio of ethyl acetate is gradually changed from 4:1 t...

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Abstract

The invention discloses an anti-hepatitis B virus active phenylpropanoids adamantine ketoxime ester compound. The structural formula of the phenylpropanoids adamantine ketoxime ester compound is shown in the description, and by conducting a HepG2.2.15 cell experiment, we find that the compound has certain inhabitation effect on HBV surface antigen (HBsAg) and e antigen (HBeAg) and is expected to prepare anti-hepatitis B virus medicines.

Description

technical field [0001] The invention relates to a series of phenylpropanoid adamantanone oxime ester compounds, as well as the synthesis of these compounds and their application in anti-hepatitis B virus activity. Specifically, it is an anti-hepatitis B virus active phenylpropanoid adamantanone oxime ester compound. Background technique [0002] Viral hepatitis type B (viral hepatitis type B), referred to as hepatitis B, is a common infectious disease caused by hepatitis B virus (Hepatitis B virus, HBV). advanced features. Hepatitis B is a serious global health problem that causes chronic liver disease and infection, and patients are at high risk of dying from cirrhosis and liver cancer. About 1 / 2 of the world's population lives in areas with high HBV infection, about 2 billion people have proven HBV infection, 300-400 million people are chronically infected with HBV, and about 780,000 people die of acute or chronic hepatitis B every year. It is the leading cause of death ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/66C07C249/12C07D317/60A61P31/20
Inventor 韦万兴刘盛周敏
Owner GUANGXI UNIV
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